Please Sir, May I Have Some More?Yet another blast from the past popped up this week, in my Yahoo IM. I’m clearly sending some sort of signal from there out to the Universe, requesting everyone I’ve rejected in the past to come around again for another beating.

This time it was The Brit and as only a few short IMs re-established, we are definitely not a dating match. We had both thought we were a physical match before, and had even had some physical-only fun once or twice after the date bombed, so upon hearing that I was single he offered that up. He’s willing to be whatever I want him to be. Oh, the power! I'm tempted to abuse it, but I just don't think I can make-out with someone I can't successfully converse with.

I’m kind of flattered, clearly I made an impression on these men that was favorable. At least I’m doing *something* right. Then again, I did meet all of them on CraigsList, and with a crap shoot like that maybe I’m just the most normal gal they’ve come across. The crap shoot goes both ways, of course, so who am I to complain?

And the Pendulum Swings Back…Last week it seemed the only men interested in reaching out to me online were men in their 40’s. This week, it’s the early twenties and students. Today alone I was instant messaged by a 23-year old (who is sure he isn’t the typical 23-year old I’m imagining, even though he’s STILL IN UNDERGRAD) and a 25-year old just back from studying at the library (he’s studying to be an actuary and taking MBA classes). At least he’s in the graduate arena of his studies.

As I briefly explained to the 23-year old, I’m looking for someone who’s in a similar stage of life as I am. Someone who has already enjoyed their irresponsible youth… someone who’s had a real job… someone who doesn’t live with his parents…

Ohhh, I knew it! I was completely spot on with the fall off in communications with Hobbes. Today I get this email that basically says he’s in love with someone else (and has been for a long time) and although she hasn’t been interested and/or the timing was off she is definitely interested, now, and so he’s going to pursue that.

He says he’s sure I’m bummed and this might be a surprise to me. Bummed? Maybe a little, but like I said I wasn’t sure whether we’d click romantically and we do have a bit of a distance issue. Surprised? Please, if I’ve learned anything in my dating adventures it’s that my gut is unbelievably accurate. I think I called this about a week ago.

He also says obviously we won’t be meeting up when I’m out there in a few weeks, since it wouldn’t be fair to lead me on if there’s something possible with someone else. Honestly? I think we could meet for drinks regardless; he can be honest about his romantic availability (or lack thereof) and still meet me for friendly drinks.

But this email feels more like I’ve been kicked to the curb. Even though he says he enjoys chatting with me and would be up for continuing if I am it’s abundantly clear in his email how his feelings for this girl obliterate any feelings for me, entirely. I 100% believe that he’d have sent the same email if this girl’s change of heart had happened after we had met up, no matter how great a time we might have had. That part stings a little, especially given some of the exchanges he and I have had as of late, but I don’t have any hard feelings. I certainly wish him the best.

I wish me the best, too. It does seem a little unfair, though.

Calvin’s Dad: The world isn't fair, Calvin. Calvin: I know, but why isn't it ever unfair in my favor?

HobbesThings have cooled off there, I think. I can’t put my finger on it, exactly, but there’s been a decrease in communications and more than once I feel like my response to something was disappointing to him. Stupid stuff, mind you, like movie references, but it’s hard not to worry a little that maybe the more he gets to know me, the less he likes me. The most damning evidence? He asked for my number over a week ago but never used it.

My gut (and my Magic 8-ball) isn’t usually wrong about these things, but I do have a tendency to over analyze so I‘m not putting much stock into it. Yet.

An Older VintageI’m starting to notice a trend in my online dating adventures… I only attract older men. Men between the ages of 39 and say 45. As a reminder, I’m 31, so this puts the dudes interested in me a solid 10 years my senior. There’s not necessarily anything wrong with a 10-year gap, but this gap in particular I think crosses dating age groups.

With this older age range, I run into a couple of issues that in and of themselves aren’t necessarily bad, but can present additional hurdles earlier in the dating scene. I don't need extra hurdles.

Like relationship status. The older one gets, the more likely one has been married previously, which for me means I at least need to cover the basics of what happened there. And then again, not being married (but wanting to be) at 40 begs the question “what’s wrong with him that he‘s never been married?”

And the children question. Ideally I would like children, all of which would be birthed before I turn the ages these men already are. Some of them aren’t sure whether they want children, possibly because the older you get the less likely you’ll be having them, and some of them already have kids, which is a whole different bag of worms. Even those that definitely want kids sort of freak me out - they could be on a much faster time line than I am.

I would never let an age gap stand in the way of a great relationship, of course, but all this older interest begs the question... what does the fact that no one my age wants to date me say? About me?!

You never bet on anything -- or anyone -- unless you're sure it's a well-calculated risk. The same holds true for today, with one exception: The universe is feeling exceptionally generous, so any risk you take will have a safety net built into it. Does this mean you'll win the lottery? Well, it might. After all, someone has to. Just don't get crazy. If you're really meant to win, one ticket will do it. Besides, some things are even better than winning the lottery. Not many, but some ....

You may not know this about me, dear readers, but I am a Scorpio. Although not a committed believer in astrology I exhibit with frightening accuracy most of the attributes of this feisty and temperamental creature. Not familiar? Here’s an overview: Scorpios are ambitious, intriguing, discerning and magnetic to others. They feel everything intensely and are able to penetrate the depths of experience. On the one hand, we’re self-sacrificing, good under pressure, and hard working. On the other, we have a tendency toward extremes, are secretive and prone to suspicion. Also we like to be in control.

It’s something I struggle with, obviously. But I have also been struggling with the Universe; while I believe that things turn out the way they should, I have been very dissatisfied with several choices the Universe has made of late. Bringing back The One That Got Away only to send him away again, going on great first dates with Marathon Guy and that new dude only to have it all go downhill from there. Even the recent communication with Hobbes has the potential to be annoying. What if I end up really liking him? Why couldn’t I have liked him anytime between now and THREE years ago when I met him (and was still emailing him)?!

But this horoscope speaks to me. Could it be that the Universe and I are headed for a truce? It's possible. I mean, at this point I would take a 2nd date with someone I find mildly attractive and who is capable of using the phone to invite me on said date as a “generous” offering. That gives the Universe a pretty wide berth with which to deliver.

And since I don’t play the lottery, except for this one time I split a ticket with a friend last year (which was not a winner, even on the rollover draw, which I am embarrassed to admit I thought would be an option for my ticket since no had won), I’ve decided I should put myself out there MORE so love can find me.

I have gone ahead and jumped on the OK Cupid bandwagon. I'm pleased to see I will be able to screen by horoscope. Scorpio women do best with Pisces men.

One of the downsides to being self-aware is, well, being aware of your self and what you’re thinking. I have always had a processing delay in my feelings, it typically runs anywhere between 12 and 24-hours when I’m presented with a situation I wasn’t expecting. For the last few days I’ve been mulling over my current situation with Hobbes, and I have come to the conclusion that I will just have to let things play out. In other words, I have to wait. I hate that.

What’s weird about it is how even though I’m thinking about it a lot, I’m not experiencing most of the anxious feelings I normally do. I don’t think emailing novel length emails every day is too much, I don’t think IMing hundreds of lines during a good portion of the work day is too much, I don’t think talking on the phone is too much, either.

I have all those early relationship feelings. Excitement when I see an email, disappointment when I don’t. That small smile when he asked how he would go about calling me this weekend (since we had already deleted each other’s phone numbers).

I feel like I should tell him. How much I enjoy spending this virtual time with him. I haven’t though, not directly. I don’t want to get ahead of myself, because I’m going to see him.

That’s right; I’ll be in his area visiting another friend in just a few short weeks. Our schedules only overlap for a small period of time, and although we’ve been unsuccessful every time we’ve tried to meet up since he moved (about 2 1/2 years ago) I think we are actually going to see each other this time.

I feel remarkably calm about the whole thing, reason enough to be alarmed given my history. We didn’t meet up in the past for a lot of perfectly good reasons, but I know at least I’ve gone away from those situations feeling a little deflated, more hurt than warranted given how we weren’t ever communicating regularly when these opportunities presented themselves. This time, though, there’s a lot of lead up. Our conversation is way past surface, there's a pretty steady undercurrent of flirtation and we’ve discussed that we both have some level of expectation and/or active interest.

It all seems totally natural to me… which is exactly why I’m worried.

He’s going to read this post, because I didn’t tell him I was writing it and not to read it (although I thought about doing that), and that doesn’t really bother me, either. I sincerely hope there is vodka nearby when my feelings about him kick in, good or bad.

I’ve been holding off on writing about my recent crush, partly because things were in a holding pattern of sorts but mostly because I was hoping things would take a turn for the better. I’m convinced now that they will not.

(him) Solid response back that he is sorry and interested and will be planning a date

Then there is a three day break in communications, in which I hope to hear from him but do not. After two and a half rounds it has become clear that whatever these messages from him say, they won’t be leading to anything involving an in-person meeting.

I’m not sure what his aim is in continuing to reach out - Does he believe the things he’s saying? Is he just trying to keep me hanging on while he tries out other ladies? - but it doesn’t matter. His actions speak louder than any text message or phone call ever could.

As for me, I’m pretty bummed about this latest disappointment, I so rarely meet someone I feel such an immediate connection with. I so rarely really put myself out there and believe someone I’ve just met. But I did believe him and now I feel like a fool.

He’s not direct, he’s not forward, and he’s definitely not interested in dating me. Oh and he shouldn’t start up a dating consulting service with his friend like he mentioned on our date. Unless he’s Exhibit A.

As is so often the case in my life, when it rains, it pours. So it is no surprise that the unexpected return of one previous suitor was quickly followed with two others. What is surprising is that which suitors returned, and that both appeared in the same few hours on a Saturday afternoon.

The WeebleLast weekend I’m lazily sitting on my couch when I get an IM notification from a handle I don’t exactly know. It looks familiar, but I can’t place it until I see the name associated with it when I allow the message. It’s the Weeble! Now, the Weeble and I went out the summer before last, so seeing an IM seems completely out of place.

We chat a bit, about our holidays and such, presents we received, the Illini game I’m watching, etc. At one point I ask him what prompted the IM (read: did you IM to ask me out?). He says he saw me online and wanted to see how my holidays were (read: I’m hoping you’ll ask me out). The chat ends agreeably, with him saying maybe we could chat again sometime.

And then we do, briefly, when he pops up again earlier this week. Things end with him telling me to let him know if I’m interested in grabbing coffee or a drink sometime. If you want to date me, Mr. Weeble, you better wobble up to the plate.

Some Other DudeAround the same time on the Saturday I get a message from this OTHER guy, who I met back in my Craigs List dating days but never actually went out with (because we’re not counting the time we met up very drunk and hooked up). He doesn’t care about what I got from Santa, he wants to come over and “massage” me. This “massage” comes with some very explicit other offerings and no expectation of reciprocation.

I declined, mostly because I wasn’t at all physically attracted to him (without all the alcohol like before) but I also think it’s really unattractive to offer your bedroom services to someone free of mutual satisfaction.

Don’t get me wrong, I don’t have an issue with casual relationships, but I do think they should be beneficial for both parties. In this case he’s saying that he knows I’m not into him, but he’ll take whatever I’ll offer him. Have some self respect, man, and stop giving your lovin’ away for free. Everyone deserves better than that.

Six months after I started this blogging adventure, and barely a month after I gave thanks that no one I had written about had found the blog, it happened. Someone I had dated, who I had written about, busted me. He emailed me (which we sometimes still do), saying he had come across my blog and was "intrigued". Before I even had a chance to decide how to respond - do I tell him about the post he’s featured in? - he wrote back this: oh, so I am TOTALLY Hobbes!

In my response I included this ridiculously run on sentence: “This is new for me. I feel a teeny bit awkward but mostly I think it's funny and I hope you don't feel bad about what I wrote and also thanks for reading and saying you like it.” What am I, twelve?

Better back and forth email ensued, in which we mostly talked about... his hair. He describes his previous, longer hair as cringe-worthy. I thought it suited him, actually, but now he’s sporting a shorter, more professional do, and also, a beard. I always did like emailing with him, never could tell where the conversation would lead us.

Back on the topic of having an open window into my dating life, he went as far as to say “Honestly reading it has made you more endearing because it demystified what little I knew about you personally and made you more human with some of the same struggles and insecurities that I have. That any of us have.”

I’m not sure about being mystifying, but he’s definitely onto something. I used to hide the things that made me feel insecure or uncomfortable from even my nearest and dearest. I felt embarrassed, I guess, and thought it would change, in a bad way, how they felt about me. As it turns out, that's crap, and writing this blog has helped me open up about everything that affects me, flattering or not. Through it I’m becoming more comfortable with who I am and that’s bettering all my relationships, not just my dating ones.

He offered to not read the blog, but it honestly doesn't bother me. I‘m glad that he gets to see who I am, if only in my dating realm. I think I'm starting to prefer the honest and upfront approach. Maybe I'm not busted, after all.

Oh and since he’s clearly not sure why I nicknamed him Hobbes in the post, it’s because of his old email signature: It's a magical world, Hobbes, ol' buddy....Let's go exploring! [Bill Watterson]

I feel like I've just gotten a swift kick in the ass. I have a new dating approach for 2010 courtesy of one of my readers, which I am posting in it’s entirety below so everyone can benefit from it's wisdom. Not sure if it’s the timing or the tone or the actual advice, but something about it made me sit up and really pay attention.

To Anonymous, I say, Yes, ma'am! And more importantly, Thanks, I think I needed that.

***I am a woman in my mid-30s whose dating life unfolded much the same as yours has (and that's why I love reading your well-written blog).

I eventually met my husband on Match (at age 36). But I didn't get anywhere with dating, or with Match, until I decided to follow a friend's simple advice: when a guy displays even a hint of weirdness or something that gives you pause or something that you just don't like, kick him to the curb! Don't analyze, don't call, don't second-guess -- just give him the boot and move on to the next guy. Listen to what your instincts are telling you!

Now you're probably thinking: "Well, shouldn't I give men a chance? Shouldn't I put myself out there? What if it's just me being scared?" Trust me, you're not going to miss out on McDreamy, and you can't rationalize away shady, rude, commitment-phobic men (i.e. Surf Dude).

I have been there. There's going to be another snowy street, and there's going to be another hand to hold, and I know you want it to be the right one. You don't need to be on "high alert". You don't need to "wait and see". He came up with some bullshit illness excuse for not attending one of the best games of the year and then has the balls to suggest (even before your second date) that you get naked? And don't even get me started on "c p", his texting-in-place-of-calling, or the absence of his name on his voice mail. He is not even worth another minute of your precious time.

I understand that the "next, please!" approach is easier said than done. I had a really, really tough time doing it at first, after so many years of giving second, third and fourth chances that turned into months of me spinning my wheels. But then I decided that if I was ever going to meet a man who would pick up the phone (not text), invite me to dinner, and then call me the next day, I had to stop wasting time on losers. As cheesy as it sounds, I actually made a list of "weird" behavior that I wouldn't tolerate. I had a lot of experience to draw on, and it helped to look back on all the patterns that inevitably emerged from men who weren't willing to pursue a healthy, long-term relationship for one reason or another.

There is a challenging, smart, funny, good-looking gentleman out there somewhere for you. I am sure of it, and I have learned in the best way possible that life can change in the blink of an eye. Now get going!

Well, 2009 certainly ended with a bang. In the past week I found out one of my interests is a decepticon, that my new crush is possibly a married drug dealer (based on reader comments) and that an ex had just read through a crap load of personal information about me after finding the blog (post on that will be out soon!). I put myself out there, so it comes with the territory, but as someone who usually feels like I’ve got the upper hand I am suddenly feeling incredibly exposed.

Exposed, but not embarrassed. These stories and musings I have about dating aren’t always flattering, but they’re mine and I try to report them impartially. Well, I do skew them a *little* in my favor, sometimes I do really stupid things in dating land. And after the laughing or crying or drinking I do I think I learn something from them.